Thermosetting resin composition and optical member using cured product of the thermosetting resin composition

ABSTRACT

The thermosetting resin composition of the present invention comprises a compound (A) containing an organic group having two or more carbon atoms and a hydrosilyl group, a compound (B) containing a carbon-carbon double bond, and a hydrosilylation catalyst (C), wherein the composition is liquid at 25° C.

TECHNICAL FIELD

The present invention relates to a thermosetting resin composition andan optical member using a cured product of the thermosetting resincomposition.

BACKGROUND ART

Generally, acrylic resins excellent in transparency and light resistancehave been heavily used as resins for optical members. On the other hand,epoxy resins have been widely used as resins for optical members usedfor the light and electronic equipment field because these resins arerequired to have heat resistance and mechanical properties in anmounting process on electronic substrates and the like and under hightemperature operation. However, in recent years, use of a high intensitylaser beam, blue colored light, and near-ultraviolet light has beenspreading also in the light and electronic equipment field, and a resinhaving better transparency, heat resistance, and light resistance thanbefore is required.

Generally, epoxy resins have high transparency in the visible region,but have insufficient transparency in the ultraviolet tonear-ultraviolet region. Among the epoxy resins, an epoxy resin preparedby using alicyclic bisphenol A diglycidyl ether or the like hasrelatively high transparency, but a disadvantage thereof is to be easilydiscolored when exposed to heat or light. As a method of solving theproblem of discoloration of such an epoxy resin, for example, PatentDocuments 1 and 2 disclose a method of reducing the impurity, which isone of the causes of the discoloration, contained in the alicyclicbisphenol A diglycidyl ether.

Further, since a cured product composed of the above alicyclic epoxy andan acid anhydride has a lower breaking strength and toughness than thatprepared by using an aromatic epoxy, interface debonding between thecured product and an adherend in a molded product and occurrence of acrack in the cured product have come to be seen as a problem.Furthermore, another problem is that the acid anhydride volatilizes atthe time of curing to reduce the volume.

Although an acrylic resin is excellent in transparency, lightdiscoloration resistance, and heat discoloration resistance, it hasinsufficient mechanical properties such as breaking strength, andfurther improvement in these properties is required. Also, anotherdisadvantage thereof is relatively large cure shrinkage, leading to avolume reduction at the time of curing.

On the other hand, since silicone resin has high transparency in theultraviolet to visible region and is excellent in light discolorationresistance and heat discoloration resistance, the use thereof in anoptical member is beginning to be investigated. However, problemsthereof are, for example, that a molded product having a complicatedshape cannot be obtained and dust and a fingerprint are liable to beattached, because silicone resin is soft. In order to improve theseproblems, for example, Patent Document 3 discloses a method ofsubstituting a part of methyl groups, which causes the softness, of thedimethylsiloxane skeleton of the silicone resin with phenyl groups. Inaddition, Patent Document 4 discloses a method of preparing a compositeof silicone resin and epoxy resin.

Patent Document 1: Japanese Patent Laid-Open No. 2003-171439 PatentDocument 2: Japanese Patent Laid-Open No. 2004-75894 Patent Document 3:Japanese Patent Laid-Open No. 2004-292807 Patent Document 4: JapanesePatent Laid-Open No. 2005-171021 DISCLOSURE OF THE INVENTION Problems tobe Solved by the Invention

However, even the methods described in Patent Documents 3 and 4 pose aproblem: the long term reliability of the resulting molded product isnot necessarily enough and interface debonding and a crack are liable tobe generated with time.

The present invention has been accomplished in view of the abovedescribed problems associated with the prior art, and an object of thepresent invention is to provide a thermosetting resin composition whichis excellent in transparency, can sufficiently reduce the cure shrinkageat the time of curing, and can sufficiently suppress the occurrence of acrack in a cured product and the occurrence of interface debondingbetween the cured product and an adherend over a long period of time,and to provide an optical member using the cured product of thethermosetting resin composition.

Means for Solving the Problems

To achieve the above object, the present invention provides athermosetting resin composition comprising a compound (A) containing anorganic group having two or more carbon atoms and a hydrosilyl group, acompound (B) containing a carbon-carbon double bond, and ahydrosilylation catalyst (C), wherein the composition is liquid at 25°C.

In the thermosetting resin composition of the present invention, thecompound (A) containing an organic group having two or more carbon atomsand a hydrosilyl group preferably has a molecular weight of from 300 to2500.

In the thermosetting resin composition of the present invention, thecompound (A) containing an organic group having two or more carbon atomsand a hydrosilyl group preferably has a silicon ratio of 0.45 or less.

In the thermosetting resin composition of the present invention, thecompound (A) containing an organic group having two or more carbon atomsand a hydrosilyl group preferably has a mass reduction percentage at200° C. of 10% or less.

In the thermosetting resin composition of the present invention, thenumber of hydrosilyl groups in one molecule of the compound (A)containing an organic group having two or more carbon atoms and ahydrosilyl group is preferably two or more.

In the thermosetting resin composition of the present invention, thecompound (A) containing an organic group having two or more carbon atomsand a hydrosilyl group is preferably liquid at 25° C.

In the thermosetting resin composition of the present invention, thecompound (A) containing an organic group having two or more carbon atomsand a hydrosilyl group is preferably a compound obtained by reacting acompound (a1) having a carbon-carbon double bond with a compound (a2)having a hydrosilyl group in the presence of a hydrosilylation catalyst(a3).

Here, the compound (a1) having a carbon-carbon double bond preferablyhas an aliphatic group and an alicyclic group.

Further, the compound (a1) having a carbon-carbon double bond preferablyhas one carbon-carbon double bond in one molecule.

In the thermosetting resin composition of the present invention, thenumber of the carbon-carbon double bonds in one molecule of the compound(B) containing a carbon-carbon double bond is preferably two or more.

In the thermosetting resin composition of the present invention, thecompound (B) containing a carbon-carbon double bond preferably has amass reduction percentage at 200° C. of 10% or less.

In the thermosetting resin composition of the present invention, thecompound (B) containing a carbon-carbon double bond is preferably liquidat 25° C.

In the thermosetting resin composition of the present invention, thecompound (B) containing a carbon-carbon double bond preferably containsat least one group selected from the group consisting of an alicyclicgroup, an aliphatic group, and a heterocyclic group.

In the thermosetting resin composition of the present invention, theequivalent ratio (hydrosilyl group/carbon-carbon double bond) of thehydrosilyl group in the compound (A) containing an organic group havingtwo or more carbon atoms and a hydrosilyl group to the carbon-carbondouble bond in the compound (B) containing a carbon-carbon double bondis preferably from 1/1.4 to 110.6.

In the thermosetting resin composition of the present invention, amixture of the compound (A) containing an organic group having two ormore carbon atoms and a hydrosilyl group and the compound (B) containinga carbon-carbon double bond is preferably transparent.

The present invention also provides an optical member comprising a curedproduct obtained by curing the thermosetting resin composition of thepresent invention.

EFFECT OF THE INVENTION

The present invention can provide a thermosetting resin compositionwhich is excellent in transparency, can sufficiently reduce the cureshrinkage at the time of curing, and can sufficiently suppress theoccurrence of a crack in a cured product and the occurrence of interfacedebonding between the cured product and an adherend over a long periodof time, and can provide an optical member using the cured product ofthe thermosetting resin composition.

BRIEF DESCRIPTION OF THE DRAWING

FIG. 1 is a schematic end view showing one embodiment of an opticalsemiconductor device provided with the optical member of the presentinvention.

DESCRIPTION OF SYMBOLS

-   -   1: Optical member, 2: Light emitting diode element, 5: Case        member, 7: Lead frame, 8: Wire, 10: Cavity, 100: Optical        semiconductor device.

BEST MODES FOR CARRYING OUT THE INVENTION

Hereinafter, a suitable embodiment of the present invention will bedescribed in detail with reference to the drawing if necessary. Notethat identical symbols are given to the same or corresponding portionsin the drawing, and overlapping descriptions are omitted.

The thermosetting resin composition of the present invention comprises acompound (A) containing an organic group having two or more carbon atomsand a hydrosilyl group (hereinafter referred to as a “component (A)” ifnecessary), a compound (B) containing a carbon-carbon double bond(hereinafter referred to as a “component (B)” if necessary), and ahydrosilylation catalyst (C) (hereinafter referred to as a “component(C)” if necessary), and the composition is liquid at ordinarytemperature (25° C.).

Conventionally, silicone resin is excellent in transparency but is poorin the compatibility (specifically, adhesion) to various members, and ithas a problem in terms of reliability. To solve this problem, in thepresent invention, an organic group having two or more carbon atoms anda hydrosilyl group are allowed to coexist in one molecule to enhance thecompatibility with an organic compound containing a carbon-carbon doublebond to obtain an organic-inorganic composite. Generally, the method forpreparing a composite of a resin as an organic substance and aninorganic substance containing silicon includes a sol-gel process in theresin and a method of separating a layer of clay in the resin. Thesemethods pose a large problem in terms of precipitation of water with theprogress of a reaction, transparency, and the like. On the other hand,it has been found that, when the thermosetting resin composition of thepresent invention containing the component (A), the component (B), andthe component (C) is thermally cured, there is no precipitateaccompanying the reaction and a highly transparent cured product isobtained. It has also been found that when the component (A) has anorganic group having two or more carbon atoms, the boiling point of thecomponent (A) increases and volatilization of a material at the time ofcuring can be suppressed. It has also been found that the cured productcan have a dense crosslinking structure and the hardness andadhesiveness with an adherend of the cured product can be improved byusing a compound containing a carbon-carbon double bond as the component(B). Thus, the thermosetting resin composition of the present inventionis excellent in transparency, can sufficiently reduce the cure shrinkageat the time of curing, and can sufficiently suppress the occurrence of acrack in a cured product and the occurrence of interface debondingbetween the cured product and an adherend over a long period of time.

Hereinafter, each component constituting the thermosetting resincomposition of the present invention will be described in detail.

The molecular weight of the compound (A) containing an organic grouphaving two or more carbon atoms and a hydrosilyl group in the presentinvention is preferably 300 or more from the viewpoint of preventing thevolatilization at the time of curing, and is preferably 2500 or lessfrom the viewpoint of ensuring compatibility with the compound (B)containing a carbon-carbon double bond. Further, the molecular weight ofthe component (A) is more preferably from 400 to 750 from the viewpointof sufficiently obtaining the above effect. When the molecular weight ismore than 750 or less than 400, control of the hardness of the resintends to become difficult.

The silicon ratio of the compound (A) containing an organic group havingtwo or more carbon atoms and a hydrosilyl group in the present inventionis preferably 0.45 or less, more preferably 0.25 or less, and furtherpreferably 0.22 or less, in order to improve the adhesion to variousmembers. Further, the silicon ratio of the component (A) is preferably0.01 or more, more preferably 0.05 or more, from the viewpoint ofcompatibility with the component (B). Here, the silicon ratio is definedas the number of silicon atoms in one molecule multiplied by the atomicweight of the silicon atom, divided by the molecular weight. Note thatthe silicon ratio is specifically calculated by the following formula:

Silicon ratio={atomic weight of silicon atom×number of silicon atoms inone molecule of component (A)}/molecular weight of component (A)

The mass reduction percentage at 200° C. of the compound (A) containingan organic group having two or more carbon atoms and a hydrosilyl groupin the present invention is preferably 10% or less, more preferably 5%or less, from the viewpoint of suppressing the loss of weight due tovolatilization of the compound at the time of curing.

The number of hydrosilyl groups in one molecule of the compound (A)containing an organic group having two or more carbon atoms and ahydrosilyl group in the present invention is preferably two or more inorder to increase the crosslinking density at the time of curing toimprove reliability. When the number of hydrosilyl groups is less thantwo, sufficient crosslinking density will not be obtained, but there isa tendency that a cured product tends to be soft.

Further, the compound (A) containing an organic group having two or morecarbon atoms and a hydrosilyl group is preferably a cyclic siliconcompound having a structure in which the hydrosilyl groups are combinedto form a ring. This enables to more sufficiently reduce the cureshrinkage at the time of curing and more sufficiently suppress theoccurrence of a crack in a cured product and the occurrence of interfacedebonding between the cured product and an adherend over a long periodof time.

The compound (A) containing an organic group having two or more carbonatoms and a hydrosilyl group in the present invention is preferablyliquid at ordinary temperature (25° C.) in view of ease of handling.

The compound (A) containing an organic group having two or more carbonatoms and a hydrosilyl group in the present invention is preferably acompound obtained by reacting a compound (a1) having a carbon-carbondouble bond (hereinafter referred to as a “component (a1)” if necessary)with a compound (a2) having a hydrosilyl group (hereinafter referred toas a “component (a2)” if necessary) in the presence of a hydrosilylationcatalyst (a3) (hereinafter referred to as a “component (a3)” ifnecessary).

Here, the compound (a1) having a carbon-carbon double bond is preferablya compound having an aliphatic group and/or an alicyclic group, morepreferably a compound having at least an alicyclic group, in terms ofpolymerization curability, transparency, and a hue. When a compoundhaving an alicyclic group is used as the component (a1), a cured productfinally obtained tends to have high transparency, low water absorption,low moisture permeability, high heat resistance, and small cureshrinkage.

The compound (a1) having a carbon-carbon double bond in the presentinvention preferably has one carbon-carbon double bond in one molecule.When the component (a1) has two or more carbon-carbon double bonds inone molecule, the component (A) which is a reaction product of thecomponent (a1) and the component (a2) will be a three-dimensionalcrosslinked body, and a mixture thereof with the component (B) tends notto be liquid but to be gel.

Examples of the compound (a1) having a carbon-carbon double bond in thepresent invention include (meth)acrylate esters such as cyclopentyl(meth)acrylate, cyclohexyl (meth)acrylate, methylcyclohexyl(meth)acrylate, trimethylcyclohexyl (meth)acrylate, norbornyl(meth)acrylate, norbornylmethyl (meth)acrylate, phenylnorbornyl(meth)acrylate, cyanonorbornyl (meth)acrylate, isobornyl (meth)acrylate,bornyl (meth)acrylate, menthyl (meth)acrylate, fenchyl (meth)acrylate,adamanthyl (meth)acrylate, dimethyladamanthyl (meth)acrylate, tricyclo[5.2.1.0^(2,6)]deca-8-yl methacrylate, cyclodecyl (meth)acrylate, methyl(meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, i-propyl(meth)acrylate, n-butyl (meth)acrylate, i-butyl (meth)acrylate, t-butyl(meth)acrylate, pentyl (meth)acrylate, n-hexyl (meth)acrylate,2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, dodecyl(meth)acrylate, lauryl (meth)acrylate, octadecyl (meth)acrylate,butoxyethyl (meth)acrylate, phenyl (meth)acrylate, benzyl(meth)acrylate, naphthyl (meth)acrylate, glycidyl (meth)acrylate,2-hydroxyethyl (meth)acrylate, nonylphenoxypolyethyleneglycol(meth)acrylate, pentamethylpiperidyl (meth)acrylate,tetramethylpiperidyl (meth)acrylate, methoxypolyethyleneglycol(meth)acrylate, N,N-dimethylaminoethyl (meth)acrylate, (meth)acryloylmorpholine, acrylamide, methacrylamide, N,N-dimethyl (meth)acrylamide,N,N-diethyl (meth)acrylamide, N,N-dimethylaminopropyl (meth)acrylamide,N-isopropyl (meth)acrylamide, N-hydroxyethyl (meth)acrylamide, and(3-(meth)acryloxypropyl) tris(trimethylsiloxy)silane; vinylenes such as4-vinylpyridine, 2-vinylpyridine, α-methylstyrene, α-ethylstyrene,α-fluorostyrene, α-chlorostyrene, α-bromostyrene, fluorostyrene,chlorostyrene, bromostyrene, methylstyrene, methoxystyrene, and styrene;maleimides such as N-methylmaleimide, N-ethylmaleimide,N-propylmaleimide, N-i-propylmaleimide, N-butylmaleimide,N-i-butylmaleimide, N-t-butylmaleimide, N-laurylmaleimide,N-cyclohexylmaleimide, N-benzylmaleimide, N-phenylmaleimide,N-(2-chlorophenyl)maleimide, N-(4-chlorophenyl)maleimide,N-(4-bromophenyl)phenylmaleimide, N-(2-methylphenyl)maleimide,N-(2-ethylphenyl)maleimide, N-(2-methoxyphenyl)maleimide,N-(2,4,6-trimethylphenyl)maleimide, N-(4-benzylphenyl)maleimide, andN-(2,4,6-tribromophenyl)maleimide; vinyl ethers such as dicyclopentenylvinyl ether, cyclohexyl vinyl ether, 1-ethyl-vinyloxy cyclohexanol,tricyclodecyl vinyl ether, a positional isomer of tricyclodecyl vinylether, tricyclodecane monomethanol vinyl ether, 9-vinyloxydicyclopentanol, vinyl monochloroacetate, vinyl pivalate, vinylbenzoate, vinyl butyrate, vinyl caproate, vinyl laurate, vinyl stearate,N-vinylacetamide, vinylcaprolactone, vinylcyclohexane,4-vinyl-1,3-dioxolane-2-one, vinylene carbonate, vinyl 2-ethylhexanoate,vinyl neodecanoate, vinyl neononanoate, 5-vinyl-2-norbornene,4-(vinyloxy)butyl stearate, and vinyl propionate; and natural productmaterials such as β-pinene and α-pinene. These can be used independentlyor in combination of two or more. Among these,tricyclo[5.2.1.0^(2,6)]deca-8-yl methacrylate, tricyclodecyl vinylether, and a positional isomer of tricyclodecyl vinyl ether arepreferred from the viewpoint of transparency, low water absorption, lowmoisture permeability, high heat resistance, and low shrinkage of acured product.

Examples of the compound (a2) having a hydrosilyl group in the presentinvention include 1,1,3,3-tetramethyldisiloxane,1,3-bis(dichloromethyl)-1,1,3,3-tetramethyldisiloxane,1,1,3,3,5,5-hexamethyltrisiloxane,1,3,5,7-tetramethylcyclotetrasiloxane,1,3,5,7,9-pentamethylcyclopentasiloxane, cyclotrisiloxane, amethylhydrosiloxane oligomer, and a hydrosiloxane oligomer. From theviewpoint of compatibility and reactivity with the component (a1),1,3,5,7-tetramethylcyclotetrasiloxane and1,3,5,7,9-pentamethylcyclopentasiloxane are particularly preferred.

The number of carbon-carbon double bonds in one molecule of the compound(B) containing a carbon-carbon double bond in the present invention ispreferably two or more in order to form a high-density three-dimensionalcrosslinking structure after curing to improve reliability. When thenumber of carbon-carbon double bonds in one molecule is less than two,the cured product tends to be soft.

The mass reduction percentage at 200° C. of the compound (B) containinga carbon-carbon double bond in the present invention is preferably 10%or less, more preferably 5% or less, in order to suppress the loss ofweight due to volatilization of the compound at the time of curing.

The compound (B) containing a carbon-carbon double bond in the presentinvention is preferably liquid at ordinary temperature (25° C.) in viewof ease of handling.

Further, the compound (B) containing a carbon-carbon double bond in thepresent invention preferably contains at least one group selected fromthe group consisting of an alicyclic group, an aliphatic group, and aheterocyclic group in terms of compatibility and hardness.

Examples of the compound (B) containing a carbon-carbon double bond inthe present invention include polyfunctional (meth)acrylates such asdicyclopentenyl (meth)acrylate, dicyclopentenyl oxyethyl (meth)acrylate,vinyl (meth)acrylate, dicyclopentadiene dimethanol di(meth)acrylate,polyethylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate,neopentyl glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate,1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate,glycerol di(meth)acrylate, 2-hydroxy-3-acryloyloxypropyl (meth)acrylate,EO adduct di(meth)acrylate of bisphenol A, and trimethylolpropanetri(meth)acrylate; arylates such as triallyl isocyanurate; vinyl etherssuch as cyclohexane dimethanol divinyl ether, cyclohexane dimethanoldivinyl ether, dicyclopentenyl vinyl ether, dicyclopentadiene dimethanoldivinyl ether, dicyclopentadiene diol divinyl ether, didecanol vinylether, tricyclodecyl vinyl ether, cyclohexyl vinyl ether,pentacyclopentadecane dimethanol divinyl ether, pentacyclopentadecanediol divinyl ether, tricyclodecane dimethanol divinyl ether,tricyclodecane diol divinyl ether, and hydrogenated bisphenol A divinylether; vinyl compounds such as divinyl adipate, vinyl crotonate, anddimethylsiloxane divinyl; and compounds having a double bond such aslimonene, 1,5-hexadiene, 1,8-nonadiene, butadiene, and polybutadiene.These can be used in combination. Among these, from the viewpoint of thehue of a cured product and the like, particularly preferred are triallylisocyanurate, tricyclodecyl vinyl ether, pentacyclopentadecanedimethanol divinyl ether, tricyclodecane dimethanol divinyl ether,hydrogenated bisphenol A divinyl ether, dicyclopentadiene dimethanoldiacrylate di(meth)acrylate, and polybutadiene.

In the present invention, the equivalent ratio (hydrosilylgroup/carbon-carbon double bond) of the hydrosilyl group in the compound(A) containing an organic group having two or more carbon atoms and ahydrosilyl group to the carbon-carbon double bond in the compound (B)containing a carbon-carbon double bond is preferably from 1/1.4 to1/0.6, more preferably from 1/1.3 to 1/0.7. When the equivalent ratio isless than 1/1.4, the carbon-carbon double bond in the component (B) willbe present excessively and the cured product tends to be discolored toreduce the transparency. When the equivalent ratio exceeds 1/0.6, thehardness of the resulting cured product tends to be reduced.

In the thermosetting resin composition of the present invention, it ispreferred that the content of the components (A) and (B) is suitablycontrolled so that the conditions of the above equivalent ratio(hydrosilyl group/carbon-carbon double bond) may be satisfied.Generally, the content of the component (A) is preferably set in therange of from 60 to 90% by mass, more preferably from 70 to 90% by masson the basis of the total amount of the components (A) and (B).

Further, in the present invention, a mixture of the compound (A)containing an organic group having two or more carbon atoms and ahydrosilyl group and the compound (B) containing a carbon-carbon doublebond is preferably transparent to visible light. When the mixtureobtained by mixing these components (A) and (B) is opaque, the resultingcured product tends to be cloudy.

In the present invention, a well-known reaction catalyst can be used forthe hydrosilylation catalyst used as the component (C) and the component(a3). Specific examples thereof include platinum group metal elementssuch as platinum (including platinum black), rhodium, and palladium;platinum chloride, chloroplatinic acid, and chloroplatinate; platinumgroup metals such as platinum black and palladium each carried by acarrier such as alumina, silica, or carbon; and a complex of platinumchloride, chloroplatinic acid, or chloroplatinate and a vinylgroup-containing siloxane, particularly a vinyl group-containingcyclosiloxane.

In the present invention, it is preferred to use a well-known catalystsuch as a platinum-based catalyst, a rhodium-based catalyst, apalladium-based catalyst for the hydrosilylation catalyst used as thecomponent (C) and the component (a3). Specific examples thereof includea platinum impalpable powder, platinum black, a platinum-carrying silicaimpalpable powder, a platinum-carrying activated carbon, chloroplatinicacid, platinum tetrachloride, a complex of chloroplatinic acid andolefin, a solution of chloroplatinic acid in alcohol, a complex ofchloroplatinic acid and an alkenyl siloxane such asdivinyltetramethyldisiloxane, a platinum-olefin complex, aplatinum-alkenylsiloxane complex, tetrakis(triphenylphosphine)palladium,a rhodium compound, and a resin powder in which any of theseplatinum-group catalysts is dispersed or encapsulated in a thermoplasticresin such as an acrylic resin, a polycarbonate resin, a silicone resin,or a polyamide resin. Among these, a platinum-containing catalyst ispreferred in terms of little discoloration. Particularly preferredplatinum-containing catalysts include chloroplatinic acid, platinumtetrachloride, a complex of chloroplatinic acid and olefin, a solutionof chloroplatinic acid in alcohol, a complex of chloroplatinic acid andan alkenyl siloxane such as divinyltetramethyldisiloxane, aplatinum-olefin complex, and a platinum-alkenylsiloxane complex.

In the thermosetting resin composition of the present invention, thecontent of the component (C) is suitably controlled by the type of thecomponent (A), the component (B), and the component (C), and the like.Generally, the content of the component (C) is preferably in the rangeof from 0.00001 to 0.5 part by mass, more preferably from 0.00001 to 0.3part by mass, relative to 100 parts by mass of the total amount of thecomponent (A) and the component (B).

Further, in addition to the above components, a hindered amine-basedlight stabilizer, a phenol-based or phosphorus-based antioxidant, anultraviolet absorber, an inorganic filler, an organic filler, a couplingagent, a polymerization modifier such as ethynylcyclohexanol, and thelike can be added to the thermosetting resin composition of the presentinvention. Furthermore, a release agent, a plasticizer, an antistaticagent, a flame retardant, and the like may be added from the viewpointof moldability.

Next, the optical member of the present invention will be described. Theoptical member of the present invention is composed of a cured productobtained by curing the thermosetting resin composition of the presentinvention as described above.

Since the optical member of the present invention is formed using thethermosetting resin composition of the present invention as describedabove, it has a sufficiently high optical transparency, and theoccurrence of a crack and the occurrence of interface debonding betweenthe member and an adherend can be sufficiently suppressed over a longperiod of time. Examples of the optical member of the present inventioninclude an optical member for optical semiconductor device applicationssuch as a transparent substrate, a lens, adhesives, an opticalwaveguide, a light emitting diode (LED), a phototransistor, aphotodiode, and a solid state image pickup device.

As a method for producing the optical member using the thermosettingresin composition of the present invention, a method of casting orpotting the thermosetting resin composition into a desired portion orpouring it into a mold and then curing it by heating can be mentioned.

As desired curing conditions, the temperature and time are selected sothat a final residual monomer may be 5% by mass or less. These curingconditions depend on types and combinations of the compound (A)containing an organic group having two or more carbon atoms and ahydrosilyl group, the compound (B) containing a carbon-carbon doublebond, and the hydrosilylation catalyst (C), and the amount of additives.The curing conditions are desirably about 1 to 10 hours at 60 to 150° C.Further, in order to reduce the internal stress generated by a rapidcure reaction, it is desirable to increase the curing temperaturestepwise.

Furthermore, in the present invention, when the component (a1) isallowed to react with the component (a2) in the presence of thecomponent (a3) in order to obtain the component (A), the reaction may beperformed by diluting the components with an organic solvent in order tosuppress the abnormal heat generation by a rapid reaction.

FIG. 1 is a schematic end view showing one embodiment of an opticalsemiconductor device provided with the optical member of the presentinvention. An optical semiconductor device 100 shown in FIG. 1 is asurface mounting type light emitting diode comprising a light emittingdiode element 2 and a transparent optical member 1 provided so that thelight emitting diode element 2 may be sealed. The light emitting diodeelement 2 is arranged at the bottom of a cavity 10 formed in a casemember 5. The light emitting diode element 2 is adhered to the casemember 5 via an adhesive layer 20 and is connected with a lead frame 7via a wire 8.

The optical member 1 covers the light emitting diode element 2 and fillsthe cavity 10. The optical member 1 is formed, for example, by a methodof pouring the thermosetting resin composition of the present inventionas described above into the cavity 10 and curing the thermosetting resincomposition in the cavity 10 by heating.

The thermosetting resin composition of the present invention asdescribed above provides a cured product thereof having sufficientlyhigh optical transparency, can sufficiently reduce the cure shrinkage atthe time of curing, and can sufficiently suppress the occurrence of acrack in the cured product and the occurrence of interface debondingbetween the cured product and an adherend over a long period of time.Further, the cured product thereof is suitable as an optical member foroptical semiconductor device applications such as a transparentsubstrate, a lens, adhesives, an optical waveguide, a light emittingdiode (LED), a phototransistor, a photodiode, and a solid state imagepickup device.

EXAMPLES

Hereinafter, the present invention will be described more specificallywith reference to Examples, but the present invention is not limited tothese.

Example 1

Into a 100 ml screw pipe were charged 6.47 parts by mass oftricyclo[5.2.1.0²′⁶]deca-8-yl methacrylate (manufactured by HitachiChemical Co., Ltd., hereinafter referred to as “TCDMA”), 3.53 parts bymass of 1,3,5,7-tetramethylcyclotetrasiloxane (manufactured by Wako PureChemical Industries, Ltd., hereinafter referred to as “TMCTS”), and0.015 part by mass of ethynylcyclohexanol (manufactured by Wako PureChemical Industries, Ltd.), followed by mixing these components toobtain a uniform mixture. Subsequently, 0.020 part by mass of a platinum(0)-2,4,6,8-tetramethyl-2,4,6,8-tetravinylcyclotetrasiloxane complex(manufactured by Wako Pure Chemical Industries, Ltd., Pt content: 1.7%by mass) was added to the mixture to obtain a solution. The solution washeated in an oven for 1 hour at 100° C., 2 hours at 125° C., and 1 hourat 150° C. to obtain a cyclic silicon compound having an organic grouphaving two or more carbon atoms and a hydrosilyl group. The resultingcyclic silicon compound was liquid in ordinary temperature (25° C.).

Next, 2.45 parts by mass of triallyl isocyanurate (manufactured byNippon Kasei Chemical Co., Ltd., hereinafter referred to as “TAIC”) and0.015 part by mass of ethynylcyclohexanol (Wako Pure ChemicalIndustries, Ltd.) were charged into the 100 ml screw pipe containing thecyclic silicon compound as described above, followed by mixing thesecomponents to obtain a uniform mixture. Subsequently, 0.020 part by massof a platinum(0)-2,4,6,8-tetramethyl-2,4,6,8-tetravinylcyclotetrasiloxane complex(manufactured by Wako Pure Chemical Industries, Ltd., Pt content: 1.7%by mass) was added to the mixture to obtain a solution of athermosetting resin composition.

The solution of the thermosetting resin composition was cast into thecavity part of a polyphthalamide surface mounting type LED having anoutside dimension of 3.2 mm×2.6 mm×1.8 mm and a cavity inside diameterof φ2.4 mm and thermally cured for 1 hour at 100° C., 2 hours at 125°C., and 1 hour at 150° C. to prepare a surface mounting type LEDpackage. In addition, 7 g of the solution of the thermosetting resincomposition were poured into an aluminum cup and heated in an oven for 1hour at 100° C., 2 hours at 125° C., and 1 hour at 150° C. to obtaincured products for measuring physical properties each having a thicknessof 3 mm and 1 mm.

Example 2

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that 6.47 parts by mass of “TCDMA” in Example 1 were replacedwith 5.97 parts by mass of tricyclodecyl vinyl ether (hereinafterreferred to as “TCD-VE”); the loading of “TMCTS” was changed to 4.03parts by mass; and the loading of “TAIC” was changed to 2.80 parts bymass, respectively.

Example 3

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that 6.47 parts by mass of “TCDMA” in Example 1 were replacedwith 5.534 parts by mass of a positional isomer of tricyclodecyl vinylether (hereinafter referred to as “TMM-VE”); the loading of “TMCTS” waschanged to 3.466 parts by mass; and the loading of “TAIC” was changed to2.395 parts by mass, respectively.

Example 4

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that 6.47 parts by mass of “TCDMA” in Example 1 were replacedwith 4.605 parts by mass of cyclohexyl vinyl ether (hereinafter referredto as “CHVE”); the loading of “TMCTS” was changed to 4.395 parts bymass; and 2.45 parts by mass of “TAIC” were replaced with 5.738 parts bymass of pentacyclopentadecane dimethanol divinyl ether (hereinafterreferred to as “PDM-DVE”).

Example 5

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that the loading of “TCDMA” in Example 1 was changed to 4.303parts by mass; the loading of “TMCTS” was changed to 4.697 parts bymass; and the loading of “TAIC” was changed to 4.868 parts by mass,respectively.

Example 6

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that the loading of “TCDMA” in Example 1 was changed to 4.948parts by mass; the loading of “TMCTS” was changed to 4.052 parts bymass; and the loading of “TAIC” was changed to 3.733 parts by mass,respectively.

Example 7

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that 6.47 parts by mass of “TCDMA” in Example 1 were replacedwith 5.274 parts by mass of n-hexyl methacrylate (manufactured byKyoeisha Chemical Co., Ltd., hereinafter referred to as “nHMA”); theloading of “TMCTS” was changed to 3.726 parts by mass; and the loadingof “TAIC” was changed to 2.574 parts by mass, respectively.

Example 8

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that 6.47 parts by mass of “TCDMA” in Example 1 were replacedwith 7.008 parts by mass of 3-methacryloxypropyltris(trimethylsiloxy)silane (manufactured by Chisso Corporation,hereinafter referred to as “TRIS”); the loading of “TMCTS” was changedto 1.992 parts by mass; and the loading of “TAIC” was changed to 1.377parts by mass, respectively.

Example 9

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that 6.47 parts by mass of “TCDMA” in Example 1 were replacedwith 6.147 parts by mass of cyclohexyl methacrylate (manufactured byKyoeisha Chemical Co., Ltd., hereinafter referred to as “CHMA”); theloading of “TMCTS” was changed to 4.395 parts by mass; and the loadingof “TAIC” was changed to 3.036 parts by mass, respectively.

Example 10

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that the loading of “TCDMA” in Example 1 was changed to 5.822parts by mass, and the loading of “TMCTS” was changed to 3.178 parts bymass, respectively; and 2.45 parts by mass of “TAIC” were replaced with4.149 parts by mass of “PDM-DVE”.

Example 11

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that the loading of “TCDMA” in Example 1 was changed to 5.822parts by mass, and the loading of “TMCTS” was changed to 3.178 parts bymass, respectively; and 2.45 parts by mass of “TAIC” were replaced with3.858 parts by mass of hydrogenated bisphenol A divinyl ether(hereinafter referred to as “HBA-DVE”).

Example 12

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that 6.47 parts by mass of “TCDMA” in Example 1 were replacedwith 4.774 parts by mass of “TCD-VE”; the loading of “TMCTS” was changedto 3.226 parts by mass; and 2.45 parts by mass of “TAIC” were replacedwith 2.95 parts by mass of tricyclodecane dimethanol divinyl ether(hereinafter referred to as “TDM-DVE”).

Example 13

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that 6.47 parts by mass of “TCDMA” in Example 1 were replacedwith 5.97 parts by mass of “TCD-VE”; the loading of “TMCTS” was changedto 4.03 parts by mass; and 2.45 parts by mass of “TAIC” were replacedwith 5.10 parts by mass of dicyclopentadiene dimethanol diacrylate(manufactured by Shin-Nakamura Chemical Co., Ltd., hereinafter referredto as “A-DCP”).

Example 14

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that 6.47 parts by mass of “TCDMA” in Example 1 were replacedwith 5.97 parts by mass of “TCD-VE”; the loading of “TMCTS” was changedto 4.03 parts by mass; and 2.45 parts by mass of “TAIC” were replacedwith 1.81 parts by mass of polybutadiene (manufactured by Aldrich,hereinafter referred to as “PB”).

Example 15

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that the loading of “TCDMA” in Example 1 was changed to 6.87parts by mass; 3.53 parts by mass of “TMCTS” were replaced with 3.13parts by mass of 1,3,5,7,9-pentamethylcyclopentasiloxane (manufacturedby Aldrich, hereinafter referred to as “PMCPS”); and the loading of“TAIC” was changed to 1.74 parts by mass.

Example 16

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that 2.45 parts by mass of “TAIC” in Example 1 were replaced with3.96 parts by mass of 1,9-nonanediol dimethacrylate (manufactured byKyoeisha Chemical Co., Ltd., hereinafter referred to as “1,9-NDA”).

Example 17

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same Trimmer as in Example 1except that the loading of “TCDMA” in Example 1 was changed to 5.822parts by mass; the loading of “TMCTS” was changed to 3.178 parts bymass; and the loading of “TAIC” was changed to 2.635 parts by mass,respectively.

Example 18

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that the loading of “TCDMA” in Example 1 was changed to 5.822parts by mass; the loading of “TMCTS” was changed to 3.178 parts bymass; and the loading of “TAIC” was changed to 3.074 parts by mass,respectively.

Example 19

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that the loading of “TCDMA” in Example 1 was changed to 5.822parts by mass; the loading of “TMCTS” was changed to 3.178 parts bymass; and the loading of “TAIC” was changed to 1.757 parts by mass,respectively.

Example 20

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that the loading of “TCDMA” in Example 1 was changed to 5.822parts by mass; the loading of “TMCTS” was changed to 3.178 parts bymass; and the loading of “TAIC” was changed to 1.317 parts by mass,respectively.

Example 21

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in Example 1except that 2.45 parts by mass of “TAIC” in Example 1 were replaced with1.59 parts by mass of “PB”.

Comparative Example 1

Into a 100 ml screw pipe were charged 3.53 parts by mass of “TMCTS” and6.47 parts by mass of “TDM-DVE” followed by mixing these components toobtain a uniform mixture. Subsequently, 0.020 part by mass of a platinum(0)-2,4,6,8-tetramethyl-2,4,6,8-tetravinylcyclotetrasiloxane complex(manufactured by Wako Pure Chemical Industries, Ltd., Pt content: 1.7%by mass) was added to the mixture to obtain a solution of athermosetting resin composition.

The solution of the thermosetting resin composition was cast into thecavity part of a polyphthalamide surface mounting type LED having anoutside dimension of 3.2 mm×2.6 mm×1.8 mm and a cavity inside diameterof φ2.4 mm and thermally cured for 1 hour at 100° C., 2 hours at 125°C., and 1 hour at 150° C. to prepare a surface mounting type LEDpackage. In addition, 7 g of the solution of the thermosetting resincomposition were poured into an aluminum cup and heated in an oven for 1hour at 100° C., 2 hours at 125° C., and 1 hour at 150° C. to obtaincured products for measuring physical properties each having a thicknessof 3 mm and 1 mm.

Comparative Example 2

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in ComparativeExample 1 except that the loading of “TMCTS” in Comparative Example 1was changed to 5.80 parts by mass; and 6.47 parts by mass of “TDM-DVE”were replaced with 4.20 parts by mass of “TAIC”.

Comparative Example 3

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in ComparativeExample 1 except that the loading of “TMCTS” in Comparative Example 1was changed to 5.24 parts by mass; and 6.47 parts by mass of “TDM-DVE”were replaced with 4.76 parts by mass of “PB”.

Comparative Example 4

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in ComparativeExample 1 except that 3.53 parts by mass of “TMCTS” in ComparativeExample 1 were replaced with 5.60 parts by mass ofpolymethylhydrosilicone (manufactured by Aldrich, hereinafter referredto as “PHS”); and the loading of “TDM-DVE” was changed to 4.40 parts bymass.

Comparative Example 5

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in ComparativeExample 1 except that 3.53 parts by mass of “TMCTS” in ComparativeExample 1 were replaced with 4.71 parts by mass of “PHS”; and 6.47 partsby mass of “TDM-DVE” were replaced with 5.29 parts by mass of “PDM-DVE”.

Comparative Example 6

A surface mounting type package and a cured product for measuringphysical properties were obtained in the same manner as in ComparativeExample 1 except that 3.53 parts by mass of “TMCTS” in ComparativeExample 1 were replaced with 1.24 parts by mass of “PHS”; and 6.47 partsby mass of “TDM-DVE” were replaced with 8.76 parts by mass of “TAIC”.

The following Tables 1 to 4 collectively show the loading of eachcomponent and the equivalent ratio (hydrosilyl group/carbon-carbondouble bond) of the hydrosilyl group in the component (A) to thecarbon-carbon double bond in the component (B) in the thermosettingresin compositions in the above Examples and Comparative Examples.

TABLE 1 Examples 1 2 3 4 5 6 7 Compo- Component TCDMA TCD-VE TMM-VE CHVETCDMA TCDMA nHMA nent (A) (a1) Loading 6.47 5.97 5.534 4.605 4.303 4.9485.274 (parts by mass) Component TMCTS TMCTS TMCTS TMCTS TMCTS TMCTSTMCTS (a2) Loading 3.53 4.03 3.466 4.395 4.697 4.052 3.726 (parts bymass) Component (B) TAIC TAIC TAIC PDM- TAIC TAIC TAIC DVE Loading 2.452.80 2.395 5.738 4.868 3.733 2.574 (parts by mass) Equivalent ratio 1/11/1 1/1 1/1 1/1 1/1 1/1 (hydrosilyl group/carbon-carbon double bond)

TABLE 2 Examples 8 9 10 11 12 13 14 Compo- Component TRIS CHMA TCDMATCDMA TCD-VE TCD-VE TCD-VE nent (A) (a1) Loading 7.008 6.147 5.822 5.8224.774 5.97 5.97 (parts by mass) Component TMCTS TMCTS TMCTS TMCTS TMCTSTMCTS TMCTS (a2) Loading 1.992 4.395 3.178 3.178 3.226 4.03 4.03 (partsby mass) Component (B) TAIC TAIC PDM- HBA- TDM- A-DCP PB DVE DVE DVELoading 1.377 3.036 4.149 3.858 2.95 5.10 1.81 (parts by mass)Equivalent ratio 1/1 1/1 1/1 1/1 1/1 1/1 1/1 (hydrosilylgroup/carbon-carbon double bond)

TABLE 3 Examples 15 16 17 18 19 20 21 Compo- Component TCDMA TCDMA TCDMATCDMA TCDMA TCDMA TCDMA nent (A) (a1) Loading 6.87 6.47 5.822 5.8225.822 5.822 6.47 (parts by mass) Component PMCPS TMCTS TMCTS TMCTS TMCTSTMCTS TMCTS (a2) Loading 3.13 3.53 3.178 3.178 3.178 3.178 3.53 (partsby mass) Component (B) TAIC 1,9-NDA TAIC TAIC TAIC TAIC PB Loading 1.743.96 2.635 3.074 1.757 1.317 1.59 (parts by mass) Equivalent ratio 1/11/1 1/1.2 1/1.4 1/0.8 1/0.6 1/1 (hydrosilyl group/carbon-carbon doublebond)

TABLE 4 Comparative Examples 1 2 3 4 5 6 Compo- Component — — — — — —nent (A) (a1) Loading — — — — — — (parts by mass) Component TMCTS TMCTSTMCTS PHS PHS PHS (a2) Loading 3.53 5.80 5.24 5.60 4.71 1.24 (parts bymass) Component (B) TDM- TAIC PB TDM- PDM- TAIC DVE DVE DVE Loading 6.474.20 4.76 4.40 5.29 8.76 (parts by mass) Equivalent ratio 1/1 1/1 1/11/1 1/1 1/1 (hydrosilyl group/carbon-carbon double bond)

The components constituting the thermosetting resin compositions, thesurface mounting type packages, and the cured products obtained in theabove Examples and Comparative Examples were measured for the followingvarious properties.

<Molecular Weight of Component (A)>

The results of the calculation of the molecular weight of the components(A) are shown in Tables 5 to 8. Note that although the silicon compoundsin Comparative Examples are compounds which contain a hydrosilyl groupand do not contain an organic group having two or more carbon atoms,they are referred to here as a component (A), for convenience.

<Silicon Ratio of Component (A)>

The results of the calculation of the silicon ratio of the components(A) are shown in Tables 5 to 8. Note that the silicon ratio is definedas the number of silicon atoms in one molecule multiplied by the atomicweight of the silicon atom, divided by the molecular weight.

<Mass Reduction Percentage of Component (A)>

The component (A) was measured for the mass reduction percentage at 200°C. Specifically, a sample of the component (A) was heated from 40° C. to200° C. (heating rate: 10° C./min) using a TG/DTA apparatus (trade name:TG/DTA 6000, manufactured by Seiko Instruments, Inc.), and the massreduction percentage was calculated from the mass at 200° C. by thefollowing equation in which the mass at 40° C. is defined as 100%. Theresults are shown in Tables 5 to 8.

Mass reduction percentage (%)={(mass at 40° C.−mass at 200° C.)/mass at40° C.}×100

<Evaluation of Transparency>

Only the components (A) and (B) were charged into a screw pipe by theratios shown in the above Tables 1 to 4 to obtain a mixed liquid, whichwas visually evaluated for the transparency by observing a fluorescentlamp through the liquid. The liquid was rated as “A” when it wastransparent and rated as “B” when it was cloudy. The results are shownin Tables 5 to 8. Note that the transparency of a cured product preparedby adding the component (C) was equivalent to the transparency of theliquid containing only the above components (A) and (B). Further, theliquid rated as “B” was not evaluated for the yellowness, interfacedebonding, and a crack because it was difficult to observe theseproperties.

<Evaluation of Yellowness>

A cured product (1 mm in thickness) for measuring physical propertieswas evaluated for the yellowness using a yellowness meter (COH 300,manufactured by Nippon Denshoku Industries Co., Ltd.). The results areshown in Tables 5 to 8. Note that the lower the yellowness, the moresuitable it is as an optical member.

<Measurement of Hardness of Cured Product>

A cured product (3 mm in thickness) for measuring physical propertieswas evaluated for the Shore hardness A using a hardness meter (a dualmeter, type A). The results are shown in Tables 5 to 8.

<Evaluation of Loss of Weight>

A surface mounting type package immediately after sealed by thermallycuring a thermosetting resin composition was visually observed for thepresence of the loss of weight by the volume decrease of the sealingresin. The package was rated as “A” when the loss of weight was notobserved and rated as “B” when it was observed. The results are shown inTables 5 to 8.

<Evaluation of Interface Debonding>

A surface mounting type package immediately after sealed by thermallycuring a thermosetting resin composition was visually observed for thepresence of the interface debonding between the sealing resin and apolyphthalamide package or a lead frame. The package was rated as “A”when the interface debonding was not observed and rated as “B” when itwas observed. The results are shown in Tables 5 to 8.

<Evaluation of Crack>

A surface mounting type package immediately after sealed by thermallycuring a thermosetting resin composition was visually observed for thepresence of a crack in the sealing resin. The package was rated as “A”when the crack was not observed and rated as “B” when it was observed.The results are shown in Tables 5 to 8.

<Evaluation of Long Term Reliability>

A surface mounting type package was subjected to 10 cycles of the coldand hot cycle test in a cold and hot cycle test machine, wherein the onecycle represents 30 minutes at −40° C. and 30 minutes at 85° C. Thesurface mounting type package after the cold and hot cycle test wasevaluated for the presence of interface debonding and a crack in thesame manner as described above. The results are shown in Tables 5 to 8.

TABLE 5 Examples 1 2 3 4 5 6 7 Molecular weight of 681 597 625 493 681681 577 component (A) Silicon ratio of 0.17 0.19 0.18 0.23 0.17 0.170.20 component (A) Mass reduction 2.1 2.3 1.8 1.8 2.1 2.1 2.3 percentageof component (A) (%) Transparency A A A A A A A Yellowness 1.2 1.5 1.62.0 1.5 1.4 2.2 Shore hardness 95 93 94 85 99 99 55 Loss of weight afterA A A A A A A curing Presence Initial A A A A A A A of After cold A A AA A A A interface and hot debonding cycle test Presence Initial A A A AA A A of crack After cold A A A A A A A and hot cycle test

TABLE 6 Examples 8 9 10 11 12 13 14 Molecular weight of 1087 577 681 681597 597 597 component (A) Silicon ratio of 0.31 0.20 0.17 0.17 0.19 0.190.19 component (A) Mass reduction 2.0 2.1 2.1 2.1 2.3 2.3 2.3 percentageof component (A) (%) Transparency A A A A A A A Yellowness 1.9 2.3 1.82.2 1.8 1.6 1.7 Shore hardness 40 65 90 95 95 93 70 Loss of weight afterA A A A A A A curing Presence Initial A A A A A A A of After cold A A AA A A A interface and hot debonding cycle test Presence Initial A A A AA A A of crack After cold A A A A A A A and hot cycle test

TABLE 7 Examples 15 16 17 18 19 20 21 Molecular weight of 741 681 681681 681 681 681 component (A) Silicon ratio of 0.19 0.17 0.17 0.17 0.170.17 0.17 component (A) Mass reduction 1.9 2.1 2.1 2.1 2.1 2.1 2.1percentage of component (A) (%) Transparency A A A A A A A Yellowness1.6 2.2 1.3 1.5 1.3 1.3 2.2 Shore hardness 89 70 99 95 99 99 72 Loss ofweight after A A A A A A A curing Presence Initial A A A A A A A ofAfter cold A A A A A A A interface and hot debonding cycle test PresenceInitial A A A A A A A of crack After cold A A A A A A A and hot cycletest

TABLE 8 Comparative Examples 1 2 3 4 5 6 Molecular weight of 241 241 2411957 1957 1957 component (A) Silicon ratio of 0.47 0.47 0.47 0.46 0.460.46 component (A) Mass reduction 100 100 100 3 3 3 percentage ofcomponent (A) (%) Transparency A B B A B B Yellowness — — _(—) 2.2 — —Shore hardness 80 — — 86 — — Loss of weight after B B B A A A curingPresence Initial — — — A — — of After cold — — — B — — interface and hotdebonding cycle test Presence Initial — — — A — — of crack After cold —— — B — — and hot cycle test

INDUSTRIAL APPLICABILITY

As described above, the present invention can provide a thermosettingresin composition which is excellent in transparency, can sufficientlyreduce the cure shrinkage at the time of curing, and can sufficientlysuppress the occurrence of a crack in a cured product and the occurrenceof interface debonding between the cured product and an adherend over along period of time, and can provide an optical member using the curedproduct of the thermosetting resin composition.

1. A thermosetting resin composition comprising: a compound (A)containing an organic group having two or more carbon atoms and ahydrosilyl group; a compound (B) containing a carbon-carbon double bond;and a hydrosilylation catalyst (C), wherein the composition is liquid at25° C.
 2. The thermosetting resin composition according to claim 1,wherein the compound (A) containing an organic group having two or morecarbon atoms and a hydrosilyl group has a molecular weight of from 300to
 2500. 3. The thermosetting resin composition according to claim 1,wherein the compound (A) containing an organic group having two or morecarbon atoms and a hydrosilyl group has a silicon ratio of 0.45 or less.4. The thermosetting resin composition according to claim 1, wherein thecompound (A) containing an organic group having two or more carbon atomsand a hydrosilyl group has a mass reduction percentage at 200° C. of 10%or less.
 5. The thermosetting resin composition according to claim 1,wherein the number of hydrosilyl groups in one molecule of the compound(A) containing an organic group having two or more carbon atoms and ahydrosilyl group is two or more.
 6. The thermosetting resin compositionaccording to claim 1, wherein the compound (A) containing an organicgroup having two or more carbon atoms and a hydrosilyl group is liquidat 25° C.
 7. The thermosetting resin composition according to claim 1,wherein the compound (A) containing an organic group having two or morecarbon atoms and a hydrosilyl group is a compound obtained by reacting acompound (a1) having a carbon-carbon double bond with a compound (a2)having a hydrosilyl group in the presence of a hydrosilylation catalyst(a3).
 8. The thermosetting resin composition according to claim 7,wherein the compound (a1) having a carbon-carbon double bond has analiphatic group and an alicyclic group.
 9. The thermosetting resincomposition according to claim 7, wherein the compound (a1) having acarbon-carbon double bond has one carbon-carbon double bond in onemolecule.
 10. The thermosetting resin composition according to claim 1,wherein the number of the carbon-carbon double bonds in one molecule ofthe compound (B) containing a carbon-carbon double bond is two or more.11. The thermosetting resin composition according to claim 1, whereinthe compound (B) containing a carbon-carbon double bond has a massreduction percentage at 200° C. of 10% or less.
 12. The thermosettingresin composition according to claim 1, wherein the compound (B)containing a carbon-carbon double bond is liquid at 25° C.
 13. Thethermosetting resin composition according to claim 1, wherein thecompound (B) containing a carbon-carbon double bond contains at leastone group selected from the group consisting of an alicyclic group, analiphatic group, and a heterocyclic group.
 14. The thermosetting resincomposition according to claim 1, wherein the equivalent ratio(hydrosilyl group/carbon-carbon double bond) of the hydrosilyl group inthe compound (A) containing an organic group having two or more carbonatoms and a hydrosilyl group to the carbon-carbon double bond in thecompound (B) containing a carbon-carbon double bond is from 1/1.4 to1/0.6.
 15. The thermosetting resin composition according to claim 1,wherein a mixture of the compound (A) containing an organic group havingtwo or more carbon atoms and a hydrosilyl group and the compound (B)containing a carbon-carbon double bond is transparent to visible light.16. An optical member comprising a cured product obtained by curing athermosetting resin composition according to claim 1.